Pokémon: 15 Most Unfairly Difficult Gym Leaders

Throughout most of the Pokémonseries, each of the games followed a strict formula for progression. The player must travel throughout the world and visit eight Pokémon Gyms. These are buildings that are staffed by professional Pokémon trainers, who act as the gatekeepers for the Elite Four. Before you can challenge the Champion of a region, you must defeat the Leaders of eight different Pokémon Gyms and claim a badge from each of them.

Not all Pokémon Gyms are created equally. If you have any sort of skill at the game, then you will likely steamroll through most of them. The true challenge in Pokémon usually does not begin until you meet the Elite Four. Despite this, there are a few Gym Leaders who are ruthlessly difficult compared to their colleagues. We are here today to name the strongest Gym Leaders of the Pokémon franchise and hopefully, give you some insight into how to beat them. From the beloved Gym Leader of Pewter City to the one rival that everyone wanted to beat.

Here are the 15 Most Difficult Pokémon Gym Leaders!

15. Brock

Brock earns a place on this list due to a very specific set of circumstances. For the most part, Brock is an absolute pushover. If you chose Bulbasaur or Squirtle in Pokémon Red & Blue, then you would beat him easily. The rematches against Brock in Pokémon Gold & Silver (and their remakes on the DS) are pretty easy also, as you battle him fairly late in the game. The changes made to the game in Pokémon Fire Red & Leaf Green also made Brock an easy challenge to overcome.

No, Brock earns a place on this list due to the challenge he presented to the poor kids who picked Charmander as their starter in Pokémon Red & Blue.

If you were new to the series, then the difficulty in the Charmander route of Gen 1 may have killed your enthusiasm for the game. Brock and his cheating Onix would have been too hard to overcome for a lowly Fire-type. There is also the fact that there are no good places to level up at this point in the game (unless you feel like fighting about a hundred level 3 Caterpies). Your choices involved spending an eternity to evolve your Charmander into a Charmeleon, raising a Caterpie into a Butterfree (so it can learn Confusion) or levelling up a Nidoran until it learns Double Kick.

14. Lenora

If you are familiar with the word “gambit”, then you likely associate it with the member of the X-Menwho throws exploding cards. The word gambit actually comes from Chess. It refers to a specific tactic, where you sacrifice a piece in order to gain some kind of advantage. This can range from a low-risk gambit (a pawn) to a high-risk gambit (a Queen).

In Pokémon Black & White, there is a Gym Leader who uses the gambit technique as part of her battle. Lenora of the Nacrene City Gym is one Game Freak’s attempts at making the Normal-type seem threatening.

Lenora is the second Gym Leader you will battle in the Unova region. She uses two Pokémon, a Herdier and a Watchog. Both of these Pokémon possess the movie Retaliate, which was introduced in the fifth generation of games. If you use Retaliate in the turn after another Pokémon on your team fainted, then its base attack will double. If either Herdier or Watchog is knocked out, then the other will perform a vicious counterattack that is likely to knock out anything you have at that point in the game. Of the two, Watchog is more dangerous, due to it knowing Hypnosis (which inflicts Sleep) and Crunch (a powerful Dark type move).

13. Brawly

Much like how the Normal-type Pokémon were considered weak in the earlier generations, Fighting-type Pokémon also got the short end of the stick. This was because Psychic-types dominated the first games in the series and Fighting-types were weak against them. Also, they couldn’t hit Ghost-type Pokémon at all with Fighting moves. You could take a single Gastly into the Fighting Dojo of Kanto and never be hit once.

As time went on, Game Freak decided to balance the game further and they made Fighting-type Pokémon more viable. The harbinger of this change was Brawly, one of the most difficult Gym Leaders in Hoenn.

In Pokémon Ruby & Sapphire, Brawly uses a Machop and a Makuhita. Both of these Pokémon know a move called Bulk Up. When a Pokémon uses Bulk Up, their Attack and Defense is raised by one stage. Brawly is one of the first Gym Leaders to abuse the hell out of stat-raising moves. He has no qualms about repeatedly using Bulk Up and squashing your team with his empowered Pokémon. He was made even more difficult in Pokémon Emerald, as he adds a Meditite to his team. This Meditite knows Light Screen and Reflect, which will further protect the team from damage.

12. Winona

Brawly is not the only formidable Gym Leader in Hoenn. In Fortree City, there lives a powerful Gym Leader, known as Winona. Of all of the Gym Leaders in the Pokémon series, she might be the most deceptive and misleading.

It is believed by fans that the reason most Gym’s use a single type or gimmick is to teach the protagonist (and by extension, the player) the rules of how battling works. If you cannot master basic things like type advantages, then you won’t stand a chance against the Elite Four.

Winona’s Gym is advertised as a Flying-type Gym. Despite this, most of her team is dual-type. She uses a Pelipper (Water/Flying), Skarmory (Steel/Flying) and Altaria (Dragon/Flying). This means that her team is far more versatile than it might first seem. In Pokémon Emerald, she adds a Tropius (Grass/Flying) to the team. If you swagger into her Gym with a grin and an Electric-type Pokémon, then you will soon be put into your place.

It also bears mentioning that Winona is a dirty cheater! Her Altaria is level 33, despite Swablu not being able to evolve into Altaria until level 35. It also knows Dragon Dance, despite Altaria not being able to learn that move until level 40. Sadly, there is no WWE Wellness Program in the Pokémon world (otherwise Lance would have been thrown in jail a long time ago).

11. Jasmine

Throughout the Pokémon series, you are generally expected to fight the eight Gym Leaders in a set order. This is because the Gym Leaders are supposed to be at a level that provides a challenge to the player (though most people throw this off by level grinding).

There are a few exceptions to the set order. A couple of the Gym Leaders can be saved for a later point in the game. One of these is Jasmine from the Johto region. It is possible to do the Team Rocket/Lake of Rage quests and fight Pryce before Jasmine, even though she is available to battle before then.

It might be wise for a player to wait until later in the game before tackling Jasmine. As the Steel-type was new to the series, Game Freak decided to make Jasmine a powerful foe in order to show how amazing these new Pokémon were.

A decent Fire-type Pokémon will take care of Jasmine’s two Magnemites. After they have fallen, she will unleash her powerful Steelix onto the field. Jasmine’s Steelix has an incredibly high defense and hit point total, which will make any fight against it into an extended slog fest. It can use Screech to lower your Pokémon’s defense score while possibly weakening it even further with Iron Tail. Jasmine’s Steelix can also spam Rock Throw, which has a very high chance of hitting.

10. Elesa

There are a handful of moves that can switch out a Pokémon. These include U-Turn (a Bug-type attack), Baton Pass (moves all stat changes from current Pokémon to the one that is being switched in) and Parting Shot (a Dark-type move that can also lower the stats of the enemy). An attack that switches out can be very effective in battle, as it can protect a Pokémon from a KO hit if it is used fast enough.

In Pokémon Black & White, a move called Volt Switch was introduced. This is an Electric-type attack that switches its user out upon completion. Volt Switch quickly became a popular move in the competitive scene, as it gave the beloved Electric-type Pokémon a new layer of strategy to their move set.

The Gym Leader of the Nimbasa Gym is based around using Volt Switch. She is called Elesa and her Gym resembles a theme park and later, a fashion runway. Elesa uses three Pokémon, all of which use Volt Switch in their arsenal. By relying on this move (plus their high speed), Elesa’s Pokémon can escape when in danger. By switching out her Pokémon after an attack, Elesa can prolong the battle, whilst raining damage down on the player.

9. Valerie

When Pokémon X & Y was released,a new breed of Pokémon, known as Fairy-type, was added to the series. The reason for this addition was unclear, though some suspect it has to do with the growing presence of online features into the series. The Nintendo DS had a hard time connecting to a lot of routers that had passwords. This, coupled with the awful Internet interface in the DS Pokémon games, meant that the series had an online mode that was more trouble to use than it was worth. When the series moved over to the Nintendo 3DS, it became a lot easier to use the online features. This meant that trading became a lot more convenient.

In the previous generations of Pokémon games, the powerful Dragon-type Pokémon were hard to find. The new online services meant that Game Freak needed a hard counter to the Dragons, as it was now really easy to get them. As such, the Fairy-type was created, to ruin the day of every fan of Dragon-type Pokémon.

With the addition of a new type to the series, a Fairy Gym was added to Pokémon X & Y. The Leader of this Gym was Valerie, a fashion designer who created Fairy themed outfits. Her team consisted of three powerful Fairies (Mr. Mime, Mawile and Sylveon). If you hadn’t learned the strengths and weaknesses of this new type, then you would have to cram and fast. If you go in with a Dragon instead of a Steel, then you are going to have a bad time.

8. Misty

Like Brock before her, Misty’s placement in the order of Kanto’s Gyms is no accident. The first generation of Pokémon games used the starter lineup as a sort of choosable difficulty mode. Bulbasaur made the game easier, as it has a type advantage against Ground and Water-type Pokémon. Squirtle is the normal difficulty, as it will be strong against Brock but have no advantages against Misty. Poor Charmander will have a difficult time against both, making him the hard mode of the game.

Misty actually presents more of a challenge than Brock, due to the fact that she uses a Starmie on her team. Throughout the series, Starmie has been one of the most overpowered Pokémon. This is due to its Water/Psychic typing and its amazing set of moves to choose from.

If you encounter Misty’s Starmie in Pokémon Red & Blue, then it will hit you with its speed-lowering Bubblebeam attack. If you fight Starmie in Pokémon Fire Red & Leaf Green, then it will now have Swift (guaranteed first hit in combat) and Recover (a healing move).

7. Tate & Liza

With a few exceptions, each Gym Leader in the Pokémon franchise is based on a single type. This extends to the theme of the Gym, as you will often see Ice-type Gyms with frozen floors, or Grass-type Gyms that are filled with foliage.

In Mossdeep City, there is a Gym that appears to cater to Psychic-type trainers. This is a facade, however, as this Gym is all about Double Battles. The third generation of Pokémon games introduced the concept of 2 on 2 Pokémon battles. This added a lot more depth and strategy to the competitive scene. It also led to the creation of moves that can apply to more than one Pokémon at a time.

The Leaders of the Mossdeep City Gym are Tate and Liza. In Pokémon Ruby & Sapphire, they only use a single Pokémon each. This means that you can concentrate your attacks on either their Lunatone or Solrock. Once one is gone, you can focus on the other.

Upon seeing that the Double Battle Gym was a letdown, Game Freak gave Tate and Liza a significant boost in Pokémon Emerald. They now had a Claydol and a Xatu on their team. The bigger team with a more diverse typing suddenly made Tate & Liza one of the biggest challenges in the game. You now have to battle a balanced team that you couldn’t beat with a simple divide and conquer strategy.

6. Fantina

Fantina is an example of a Gym Leader who was made significantly easier in the updated version of her generation.

Gengar is considered by many to be the best Ghost-type Pokémon in the series. This isn’t just Gen 1 nostalgia talking either, as it sees a lot of play in the competitive scene. Game Freak seems to agree, as Gengar appears on the roster of every Ghost-type Gym Leader in the series. Fantina is no exception to this, as she uses a powerful Gengar on her team, that is loaded up with status effect moves. If you can get past Gengar, you then have to fight an equally powerful Mismagius, that has several strong attacks in its arsenal.

When Pokémon Platinum was released, the battle against Fantina happens a lot sooner. As such, her team was significantly weakened. Her entire team had its level dropped by ten and her Gengar was now a Haunter. The Drifblim she previously used as an opener was now replaced with a Duskull.

5. Lt. Surge

Lt. Surge is best known for the fan-favourite episode of the Pokémon anime, where Ash considers evolving Pikachu in order for it to be strong enough to face against Surge’s Raichu. He is also known for being a key part of the “Pokémon takes place after a war” fan theory, due to Surge being described as an American who fought during a war in the past.

In Pokémon Red & Blue, Lt. Surge provides a decent challenge for players. That is, unless, you have raised a Ground-type Pokémon. Due to Ground-type’s immunity to Electric-type moves, Lt. Surge will have no options in battle.

When Pokémon Fire Red & Leaf Green were released, they made Lt. Surge a lot more challenging. This is because his Pikachu and Raichu now had Double Team in their arsenal and weren’t afraid to use them. Double Team increases the evasion of the Pokémon that uses it, making them harder to hit. After a couple of Double Teams, the battle will devolve into constant misses. If you bring a Ground-type Pokémon into the battle, then you will have a better chance at victory. Surge’s Pikachu and Raichu now possess Quick Attack, however, which would force an annoying battle of attrition between them and a Ground-type Pokémon.

4. Whitney

In the first generation of Pokémon games, the only Normal-type Pokémon worth a damn were Snorlax and Chansey. The Normal-types were almost totally useless at the start of the series and the fans knew it.

From that point on, Game Freak decided to create a few brutally difficult Normal-type Gyms in order to prove that they could be powerful too. Lenora fought with an interesting tactic in Pokémon Black & White, but she pails in comparison to her contemporaries in Johto and Hoenn.

Whitney is the 3rd Gym Leader of the Johto region in Pokémon Gold & Silver. She has gained a reputation as one of the most difficult Gym Leaders in the entire franchise. This all comes down to her murderous Miltank, who has sent many trainers back to New Bark Town with their tails between their legs.

The Miltank used by Whitney has a devastating array of moves and the high stats to back them up. Stomp is a powerful attacking move. Attract will make all-male Pokémon miss their attacks 50% of the time. Milk Drink is a healing move. The final weapon in Miltank’s arsenal is Rollout, a move that gains power for every consecutive turn it hits. This forces players to end the battle against Whitney quickly before the Rollout becomes unstoppable.

3. Norman

Norman of the Petalburg City Gym believes in the Spartan approach to child rearing. Instead of giving his kid a free pass to the Pokémon League, he makes them fight two giant gorillas.

In Game Freak’s continuing quest to make Normal-type Pokémon seem scary, the fifth Gym of Pokémon Ruby & Sapphire belonged to them. The Gym Leader, Norman, is also the father of the protagonist. In fact, he is the only father of any protagonist in the series that is seen in-game. Despite being his flesh and blood, Norman won’t allow the player to challenge him until they have four other Gym badges.

The battle against Norman in Pokémon Ruby & Sapphire is an all-out war against his troupe of fighting apes. He uses two (illegally levelled) Slakings, as well as a Vigoroth. Slaking is kind of like the Hoenn version of Snorlax. It has incredible stats, but won’t act every other turn. Good luck trying to chip away at these beasts, as they slam into you with powerful attacks. Vigoroth isn’t quite as powerful, but it lacks the off-turn weakness.

Norman was made easier in Pokémon Emerald, as one of his Slaking’s was replaced with a Spinda and a Linoone. He does love his kid after all!

2. Clair

If you ignore the fact that he is a dirty cheater, then there is no denying that Lance is a powerful Pokémon trainer. It seems that it runs in the family, as his cousin is one of the most challenging Gym Leaders in the entire series.

The final Gym in Johto resides in Blackthorn City. It is a Dragon-type Gym that is led by a lady named Clair. As the Fairy-type had not been introduced yet, your only effective weapon against Dragons was Ice-type Pokémon or other Dragons. As such, you will likely be unprepared to deal with the denizens of Clair’s Gym. Even the regular grunt trainers who hang out in the Blackthorn City Gym are a challenge to fight. You will need a lot of healing items prepared, as you will want to be on top form for when you finally encounter Clair.

In Pokémon Gold & Silver, Clair uses three Dragonairs on her team. Each of them has a few unique moves, as well as the powerful Dragonbreath attack. The real challenge comes when you battle Kingdra. Due to Kingdra being a Water/Dragon-type, it loses the weakness to Ice moves. This means that your only effective attack against Kingdra will be Dragon-type moves. It is actually impossible to get a Dragon-type Pokémon at that point in the game without trading.

Clair’s Kingdra is one of the most difficult challenges in the game. Kingdra’s high stats, powerful moves and resistances will make it a match for your entire team.

1. Blue

In the Pokémon Origins anime, it is established that a Gym Leader will only use an amount of Pokémon that is equal to the experience of the trainer who is making the challenge. Brock is shown to only choose two Pokémon when he discovers that Red has yet to win any Gym badges.

Of all of the Gym Leaders in the Pokémon franchise, only one of them truly cuts loose and unleashes a balanced and varied team on his first match with the player. His name is Blue, but fans know him better as Gary Oak.

After the Viridian City Gym is abandoned by Giovanni (after his ties to Team Rocket are revealed), the former Champion of the Kanto region takes over as the Leader. Blue is unique in a few regards. He is the only Gym Leader to use six Pokémon during your first battle against him. Blue has no type preferences, meaning you are essentially fighting a Champion level team in his Gym. His level 60 Pidgeot is also the highest level Pokémon used by any Gym Leader during your first battle against them. The rematch against Blue is even harder, as he changes a few of the Pokémon in his team, by adding a Rhyperior and a Tyranitar to his arsenal.

Blue was a pain to fight when he was your rival. As a Gym Leader, he is truly a force to be reckoned with.